In high school Jen and I were besties, inseparable, “BFFs”. I know the jokes about how that never lasts, but I think we’ve fared better than most. I’ve known her since our early teens and to this day we still keep in touch. It’s been rough since she moved for university, I miss my best friend, but I’m also happy that she’s doing something she loves. I wasn’t sure what I wanted to do in life so I’ve been working at a dog spa since graduation, it’s not ideal but I enjoy the work.
Jen’s house was always *the* spot to hang out. I grew up in small row house apartment with two older siblings and I never felt like I had much space. I used to love hanging out at Jen’s place, she had a whole basement to herself with her own TV and there was a pool in the back yard. Her parents were even okay with us drinking or smoking pot so long as things didn’t get too crazy.
I think about those times often now that we don’t get to see each other as much anymore. That’s why I was so excited that Jen was coming back for a few weeks in the summer, I couldn’t wait to see her and hang out like old times.
Her parent’s were as welcoming as ever, maybe even more than before because they were so happy to have us there again. Her mom was her usual bubbly self, always out and about shopping or meeting friends for lunch, or busy working on hobbies. Her dad was still a gracious hosting, bringing out drinks and snacks for us. I noticed his hair was certainly more greyed than I remember but he looked younger with his beard neatly trimmed.
He had just brought us a few drinks when his phone rang and he answered and went inside. I went in shortly after to use the bathroom and as I was walking down the hall I could hear him on the phone in his office. The door was closed except for a crack and I overheard him. I don’t make a habit to eavesdrop but he sounded distressed and upset and I couldn’t really help myself.
“It’s been MONTHS Sheila! The therapist explained how we could make progress on this…”
I instantly felt bad for listening in so I quietly went to the bathroom down the hall. As I emerged I heard him yell into the phone “I’m not going another year! I’m not a fucking eunuch! I’ve done everything you asked. Can we please…. hello?… Hello?” It sounds like Sheila hung up on him.
I snuck back past his closed office door towards the kitchen then back outside. I could hear his words echo in my head, I always though their marriage was so idyllic. I felt sorry for him, Jen always gushed about how amazing her dad was and realizing he was secretly so frustrated was kind of heartbreaking.
When he came outside he was his usual friendly self, as if nothing had happened! I began to wonder how long he’s been pretending he’s okay….
It became a beautiful afternoon as the clouds finally rolled away, I peeled off my sarong and top so I could sunbath and take a dip in the pool. I wore a new two piece white bathing suit I got cheaply online. I laid on my stomach on a lounger and pick up my phone, but before turning it on I see in the reflection of the glass that her dad staring at me from across the pool. I thought about his phone conversation and I realized he’s probably stuck in a sexless marriage… and here I am parading around in a swimsuit that would barely pass for underwear.
At first I tried to be more modest. I sunbathed and swam as I normally did but was conscious of what he might possibly see. I could tell that he’d stare at my ass or catch a glimpse of my chest when I walked by. At first it was strange, he’d known me since I was a teen, but now I just felt sorry for him. I could sense he was conflicted, he’d catch himself staring and you could sense the level of focus he was putting towards looking anywhere but me. I tested him be knocking over my bag so I’d bend over to pick it up, then I’d glace behind me to see him fixated on my ass.
I walked by again towards my chair when he suddenly got up and went inside. I told Jen I’d be right back and I got up and went inside after him. His office door was closed and I stood outside for a moment about to knock, then thought better of it. I was about to turn around and go back outside when I heard soft moans through the door. Without thinking I swiftly swung open the door. Will was sitting at his desk, his shorts at his ankles and cock in hand, jerking off to pictures of bikini girls on his computer. “BETH!” he called as he scrambled to cover himself and close his computer. “I… umm… ” He was at a loss for words. I stood there a moment then slowly closed the door behind me.
“Will…. ” I say softly. “I overheard you on the phone earlier… I’m sorry.” I take a step towards him as he scrambles to do up his belt buckle. I look him in the eyes. “I saw you staring at me outside… and wanted to say… *It’s Okay*.” I’m not sure why I came in after him, I guess felt sorry for him, but I decided to let him have a good look. “You can stare… I don’t mind.” I smile and turn around and pose to show off my ass before I spin back around. I lean forward and press my breasts together under my triangle bikini top. “Isn’t this what you wanted to see?” I ask him as he stares at me stunned. I lick a finger and slip my hand under my bikini bottoms and rub myself as I squeeze my breast.
“Oh fuck… ” he whispers as he begins rubbing himself through his shorts. “You are so god damned sexy…. I’d give anything to see tits like yours…” He adds nervously. I laugh and look around his room and notice a bottle of expensive tequila on the bar next to his desk. “I’ll tell you what.” I say and point at the bottle I could never afford for myself. “Give me that bottle of tequila and I’ll loose the top.” My thumbs slide under the neck strap as I tease. “It’s yours! I’ll buy you a new one!” he replies without hesitation. His breathing is heavy and his mouth gapes open as he stares at me. I figured a little voyeurism is harmless. “Deal” I say with a huge smile and I pull the tie strap and my top falls away.
He takes his cock out of his shorts and begins to stroke and seconds later he starts to grunt as he holds a tissue to himself as he cums while staring at my breasts. I smile, genuinely pleased with myself and begin to put my top back on before quietly leaving while I whisper “You owe me… ” I went back to sunbathing and he came back out 20 minutes later and I saw him sit back and relax on the lounger with a satisfied grin.
I inadvertently kickstarted a sexual relationship with Will. We’ve visited alone a few times since our fun at the pool and each time he’s masturbated as he’s watched me strip and pose. It was a good deal, honestly. He’s never even seen me fully naked and still offers me booze or gift cards which I gladly accept. I was just enjoying the attention, but the gifts were a fun bonus. I was not prepared for when he showed up today at my apartment.
My doorbell rings and I answer, I’m a little surprised that Will’s on my doorstep. I joke about whether he’s got another bottle of booze for me which makes him grins nervously while he comes inside. “Beth… ” he says so nervously his voice is cracking. “I… haven’t been with anybody in…um.. years. I umm… wanted to… Would you…. you know. With me? What will it take?” Shocked I stand staring at him. “What?” I ask again.
“I haven’t had sex in years. Please… I’ll pay anything. I… don’t know what else to do.” He looks nervous and shy, I feel sorry for him. “I have money.” He says softly. “I know you aren’t a…. well you know. But I want to help you too.” He pulls out a pile of cash and holds it out in front of him. “This is 800$ in cash. It’s all I could get without anybody noticing. ” I stare at him silently as I contemplate how I got here, this feels so far from our playful voyeurism in exchange for a gift here or there. He’s never even seen me naked. But holly fuck is that a pile of cash! I’ve lost track of how many losers I’ve fucked out of convenience, getting paid never even occurred to me.
I stand silently staring at the money for what felt like an eternity. “I… I should go” He says as he turns towards the door. “No. wait” I call. “Are you for real?” I ask in a serious tone. He nods yes and holds out the money. I take it and ruffle through it, it looks real enough. I look back up at him, he looks pathetic but smiles hopefully. I grip the cash and close my eyes. “What do you want to do?” I ask as I look back up at him. “I just want to be touched again. Sex. Just sex. You don’t have to do anything you aren’t comfortable with. I just need to feel what it’s like again.”
I look down at the pile of cash and there was a long silence. “Okay.. I’ll do it.” The words fall out of my mouth and I start to feel numb. My gaze is cast a million miles away and I reach out to grab his hand and I walk him to my bedroom. It’s a mess with clothes on the floor and bed but neither of us care. I motion for him to sit on the edge of the bed and I take a step back. I begin to strip like I’ve done before then hesitate a moment before I peel off my underwear. Suddenly it feels real, I’m nervous and shy, way more than with any new partner before. Will compliments my body as he strips himself, he gushes about my clean shaven pussy and perky breasts.
I walk towards him and reach my hands out and pull his head against my chest. He nestles his face between my tits as his hands grip my ass. “Lean back” I say as I climb down on my knees and hesitantly grab his cock. He’s trimmed and already hard. I lean in and gently kiss the head of his cock as he moans loudly. “OH god .. fuck!” He calls out as my lips slide down the head of his cock. He breaths heavy and deeply and suddenly calls “wait.. wait wait..” then holds my head still.
I pull my head back as he lets go and he falls back onto the bed. “Do you have a condom?” I ask. He lifts his head and looks at me like he’s almost in a daze “I’m fixed… if that’s what you are worried about.” I’ve never fucked a new partner without a condom before, but he hasn’t had sex in years so I wasn’t worried. I climb on top facing him then lick my finger and begin to play with myself, then I grab his cock and guide it against me as my pussy envelopes his cock. “Oh god. Oh god!” he calls out as he grabs my breast and ass as he thrusts a few times and seems to cum. I sit on him, stunned. His arms fall away wide to his sides and his head falls back as he catches his breath.
“Was that it?” I ask with genuine surprise as he turns beet red and grimaces. “I took some help” he admits… “How long have we got?” I glance at the clock on my bedside table “I should probably leave for work in 30 minutes.” I say “That should work.” he replies. I roll off him and he stares at me as I grab a towel to wipe myself before I pass it to him. He wipes his cock and begins to play with himself again. “Would you… bend over the bed?” he asks. I shrug and drop my elbows onto the bed next to him and spread my legs and wiggle my ass. I’ve never fucked somebody this old, I thought maybe some teasing would help him get hard again.
He stands behind me and curses as he squeezes and slaps my ass. I feel the tip of his cock rub back and forth across my pussy before sliding into me. He grips my hips with both hands and slowly begins a few shallow thrusts. He kicks my feet further apart and uses his weight to pin my back to the bed, I moan with excitement. “You like that?” he says and I nod yes. He reaches for my arms and pulls them behind me and holds my wrists together with his big strong hand while he slaps my ass and fucks me rhythmically. My helpless position and his hard thrusting overwhelm me and I begin to moan loudly as I approach climax. I groan as I cum which encourages him to pin me tighter and deliver a few final hard thrusts before he explodes again and falls forward to collapse next to me.
I close my legs and fumble for the towel and head to the bathroom to clean up. When I come back out he’s mostly dressed. “I’ve left it for you on the kitchen table” he says shyly, then adds “I have to go” and he grabs his stuff and leaves.
I walk to the kitchen, I’m naked and gooey and my ass is sore, but there on the table is a stack of 50$ bills. I pick them up and ruffle through them, it’s all there like he said. I stand staring at the cash for a while then pull out my phone and walk to the bathroom. I pose with one foot on the tub and my arm across my tits, while holding a 50$ bill to cover my pussy. I snap a selfie of my shoulders down and text it to Will. “1000$ next time.”
Source: reddit.com/r/eroticliterature/comments/xoq39a/f20_transactional_sex_and_my_best_friends_dad_m55